Highly efficient cross-coupling reactions with the perfluoroorganotrifluoroborate salts K [RFBF3] (RF=C6F5, CF2CF)

Synthesis of molecular tweezers bearing pentafluorophenyl and several pendant aryl groups

“…The coupling reaction of 6b with C 6 F 5 B(OH) 2 under the usual conditions (Pd(PPh 3 ) 4 , K 2 CO 3 , DME, 70 8C for 12 h) did not proceed as was expected (Table 1). Next, we tried the coupling reaction under the Frohn's condition [9]. However, our attempts for the coupling reaction of dibromide 6b with C 6 F 5 BF 3 K gave no product (Table 1).…”

“…Recently, Pd-catalyzed and Ag 2 O-promoted coupling reactions of C 6 F 5 BF 3 K with aryl iodides have been reported by Frohn et al (Eq. (3)) [9]. Although the reaction yielded the coupling products in more than 90% yield, the method was not applicable to aryl bromides.…”

Potassium Organotrifluoroborates: New Perspectives in Organic Synthesis

“…162 The presence of K 2 CO 3 is not essential using Ag 2 O, but it seems to prevent hydrodeboronation of the trifluoroborate salt. 162 Cross-coupling with potassium pentafluorophenyltrifluoroborate was applied to the preparation of molecular tweezers.…”

Palladium-Catalyzed Cross-Coupling Reactions of Perfluoro Organic Compounds

“…Pd(0)-catalyzed cross-coupling reactions of trifluorovinylzinc, tin, or borate reagents emerged in the 1980s as more direct synthetic methods [24][25][26][27][28][29][30][31][32][33]. A synthetic route involving a more stable trifluorovinyl borate has recently been developed to replace the zinc or tin reagents [34,35]. Alternative routes to synthesize (α,β,β-trifluoro)styrenes via the cross-coupling of chlorotrifluoroethylene with arylboronic acids have recently been reported [36,37].…”